Synthesis of target-specific radiolabeled peptides for diagnostic imaging

Bioconjugate Chemistry

Volumn 14, Issue 1, 2003, Pages 3-17

  Fichna, Jakub ^a   Janecka, Anna ^a  

^a MEDICAL UNIVERSITY OF LODZ   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

PEPTIDES;

DIAGNOSTIC IMAGING;

BIOCHEMISTRY;

1 (1 CARBOXY 3 CARBO TERT BUTOXYPROPYL) 4,7 (CARBO TERT BUTOXYMETHYL) 1,4,7 TRIAZACYCLONONANE; 1,4,7 TRIAZACYCLONONANE 1,4,7 TRIACETIC ACID; 1,4,7 TRIAZACYCLONONANE N,N',N'' TRIS(METHYLENEPHOSPHONATE MONOETHYL ESTER); 1,4,7 TRIAZACYCLONONANE N,N',N'' TRIS(METHYLENEPHOSPHONIC)ACID; 1,4,7,10 TETRAAZACYCLODODECANE 1,4,7,10 TETRAACETIC ACID; 2 HYDRAZINONICOTINIC ACID; ALPHA INTERMEDIN DERIVATIVE; BOMBESIN DERIVATIVE; NEUROTENSIN DERIVATIVE; NICOTINIC ACID DERIVATIVE; PENTETIC ACID; RADIOPHARMACEUTICAL AGENT; SUBSTANCE P DERIVATIVE; UNCLASSIFIED DRUG; VASOACTIVE INTESTINAL POLYPEPTIDE DERIVATIVE;

CHELATION; COVALENT BOND; DIAGNOSTIC IMAGING; DRUG STRUCTURE; DRUG SYNTHESIS; ISOTOPE LABELING; PEPTIDE SYNTHESIS; REVIEW;

EID: 0037262667     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc025542f     Document Type: Review

References (177)

1. Hoefnagel, C. A. (1991) Anticancer radiopharmaceuticals. Anticancer Drugs 2, 107-132.
2. Schubiger, P. A., Alberto, R., and Smith, A. (1996) Vehicles, chelators, and radionuclides: choosing the "building blocks" of an effective therapeutic radioimmunoconjugate. Bioconjugate Chem. 7, 165-179.
3. Reubi, J. C. (1995) Neuropeptide receptors in health and disease: the molecular basis for in vivo imaging. J. Nucl. Med. 36, 1825-1835.
4. Verbruggen, A. M. (1990) Radiopharmaceuticals: state of the art. Eur. J. Nucl. Med. 17, 346-364.
5. Antar, M. A. (1990) Radiopharmaceuticals: state of the art. Nucl. Med. Biol. 17, 103-128.
6. Pauwels, E. K., McCready, V. R., Stoot, J. H. M. B., and van Deurzen, D. F. P. (1998) The mechanism of accumulation of tumour-localising radiopharmaceuticals. Eur. J. Nucl. Med. 25, 277-305.
7. Wessels, B. W., and Meares, C. F. (2000) Physical and chemical properties of radionuclide therapy. Semin. Radiat. Oncol. 10, 115-122.
8. Liu, S., and Edwards, D. S. (1995) Technetium and Rhenium in Chemistry and Nuclear Medicine (Nicolini, M., Banoli, G., Mazzi, U., Eds.) pp 383-393, SG Editoriali, Padova.
9. Park, C. H. (1997) The role of radioisotopes in radiation oncology. Semin. Oncol. 24, 639-654.
10. Saha, G. B., Go, R. T., and Macintyre W. J. (1992) Radiopharmaceucticals for cardiovascular imaging. Nucl. Med. Biol. 19, 1-20.
11. Walovitch, R. C., Williams, S. J., and Lafrance, N. D. (1990) Radiolabeled agents for SPECT imaging of brain perfusion. Nucl. Med. Biol. 17, 77-83.
12. Nunn, A. D. (1990) Radiopharmaceuticals for imaging myocardial perfusion. Semin. Nucl. Med. 20, 111-118.
13. Britton, K. E. (1990) The development of new radiopharmaceuticals. Eur. J. Nucl. Med. 16, 373-385.
14. Eckelman, W. C. (1994) The application of receptor theory to receptor-binding and enzyme-binding oncologic radiopharmaceuticals. Nucl. Med. Biol. 21, 759-769.
15. Seregni, E., Chiti, A., and Bombardieri, E. (1998) Radionuclide imaging of neuroendocrine tumours: biological basis and diagnostic results. Eur. J. Nucl. Med. 25, 639-658.
16. Schmidt, M., Scheidhauer, K., Luyken, C., Voth, E., Hildebrandt, G., Klug, N., and Schicha, H. (1998) Somatostatin receptor imaging in intracranial tumours. Eur. J. Nucl. Med. 25, 675-686.
17. Spencer, R. P. (1991) Receptor-mediated radiopharmaceutical imaging of the liver. Targeted Diagn. Ther. 4, 321-338.
18. Volkert, W. A., and Hoffmann, T. J. (1999) Therapeutic radiopharmaceuticals. Chem. Rev. 99, 2269-2292.
19. Weiner, R. E., and Thakur, M. L. (2001) Radiolabeled peptides in diagnosis and therapy. Semin. Nucl. Med. 31, 296-311.
20. Lister-James, J., Moyer, B. R., and Dean, R. T. (1990) Small peptides radiolabeled with 99mTc. Q. J. Nucl. Med. 40, 221-233.
21. Eckelman, W. C. (1995) Radiolabeling with technetium-99m to study high-capacity and low-capacity biochemical systems. Eur. J. Nucl. Med. 22, 249-263.
22. 99mTc-labeled small peptides as diagnostic radiopharmaceuticals. Chem. Rev. 99, 2235-2268.
23. Jurisson, S. S., and Lydon, J. D. (1999) Potential technetium small molecule radiopharmaceuticals. Chem. Rev. 99, 2205-2218.
24. Hnatovich, D. J. (1990) Recent developments in the radiolabeling of antibodies with iodine, indium, and technetium. Semin. Nucl. Med. 20, 80-91.
25. Schwochau, K. (1994) Technetium radiopharmaceuticals - fundamentals, synthesis, structure and development. Angew. Chem., Int. Ed. Engl. 33, 2258-2267.
26. 99mTc labeling of highly potent small peptides. Bioconjugate Chem. 8, 621-636.
27. Okarvi, S. M. (1999) Recent developments in 99mTc-labeled peptide-based radiopharmaceuticals: An overview. Nucl. Med. Commun. 20, 1092-1112.
28. Hom, R. K., and Katzenellenbongen, J. A. (1997) Technetium-99m-labeled receptor-specific small-molecule radiopharmaceuticals: recent developments and encouraging results. Nucl. Med. Biol. 24, 485-498.
29. Okarvi, S. M. (2001) Recent progress in fluorine-18 labeled peptide radiopharmaceuticals. Eur. J. Nucl. Med. 28, 929-938.
30. Anderson, C. J., and Welch, M. J. (1999) Radiometal-labeled agents (non-technetium) for diagnostic imaging. Chem. Rev. 99, 2219-2234.
31. Srivastava, S. C., and Mease, R. C. (1991) Progress in research on ligands, nuclides and techniques for labeling monoclonal antibodies. Int. J. Rad. Appl. Instrum. B. 18, 589-603.
32. Fischman, A. J., Babich, J. W., and Strauss, W. (1993) A ticket to ride: Peptide radiopharmaceuticals. J. Nucl. Med. 34, 2253-2263.
33. Ehrhardt, G. J., Ketring, A. R., and Ayers, L. M. (1998) Reactor-produced radionuclides at the University of Missouri Research Reactor. Appl. Radiat. Isot. 49, 295-297.
34. Langer, M., and Beck-Sickinger, A. G. (2001) Peptides as carrier for tumor diagnosis and treatment. Curr. Med. Chem.- Anti-Cancer Agents 1, 71-93.
35. Thakur, M. L. (1995) Radiolabeled peptides: Now and the future. Nucl. Med. Commun. 16, 724-732.
36. Katzenellenbogen, J. A. (1995) Designing steroid receptor-based radiotracers to image breast and prostate tumors. J. Nucl. Med. 36(Suppl), 8S-13S.
37. 99mTc-labeled chemotactic peptides for studies of inflammation in vivo. Bioconjugate Chem. 9, 208-217.
38. 188Re-RC-160, a directly radiolabeled somatostatin analogue. Int. J. Cancer 65, 214-220.
39. Thakur, M. L. (1993) Tc-99m labeled sandostatin: preparation and preliminary evaluation. J. Labeled Cmpd. Radiopharm. 32, 365-367.
40. Lister-James, J., Vallabhajosula, S., Moyer, B. R., Pearson, D. A., McBride, B. J., De Rosch, M. A., Bush, L. R., Machac, J., and Dean, R. T. (1997) Pre-clinical evaluation of technetium-99m platelet receptor binding peptide. J. Nucl. Med. 38, 105-111.
41. Lister-James, J., Knight, L. C., Maurer, A. H., Bush, L. R., Moyer, B. R., and Dean, R. T. (1996) Thrombus imaging with a technetium-99m-labeled, activated platelet receptorbinding peptide. J. Nucl. Med. 37, 775-781.
42. Eckelman, W. C. (1990) Development of radiochemically pure antibodies. Cancer Res. 3, 686-692.
43. Delmon-Moingeon, L. I., Mahmood, A., Davison, A., and Jones, A. G. (1991) Strategies for labeling monoclonal antibodies and antibody-like molecules with technetium-99m. J. Nucl. Biol. Med. 35, 47-59.
44. Eisenwiener, K. P., Powell, P., and Maecke, H. R. (2000) A convienent synthesis of novel bifunctional prochelators for coupling to bioactive peptides for radionuclide labeling. Bioorg. Med. Chem. Lett. 10, 2133-2135.
45. Anderson, G. W., Zimmerman, J. E., and Callahan, F. M. (1967) A reinvestigation of the mixed carbonic anhydride method of peptide synthesis. J. Am. Chem. Soc. 89, 5012-5017.
46. Anderson, G. W., Zimmerman, J. E., and Callahan, F. M. (1964) The use of esters of N-hydroxysuccinimide in peptide synthesis. J. Am. Chem. Soc. 86, 1839-1842.
47. Grumbach, I. M., and Veh, R. W. (1991) Sulpho-N-hydroxysuccinimide activated long chain biotin. A new microtitre plate assay for the determination of its stability at different pH values and its reaction rate with protein bound amino groups. J. Immunol. Methods 140, 205-210.
48. 188Re labeling of amines and peptides. Technetium and Rhenium in Chemistry and Nuclear Medicine 4. (M. Nicolini, G. Bandoli, U. Mazzi, Eds.) pp 363-366, SGEditoriali, Padua.
49. Meares, C. F. (1986) Chelating agents for the biding of metals to antibodies. Nucl. Med. Biol. 13, 311-318.
50. McMurry, T. J., Pippin, C. G., Wu, C., Deal, K. A., Brechbiel, M. W., Mirzadeh, S., and Gansow, O. A. (1998) Physical parameters and biological stability of yttrium(III) diethylene-triaminepentaacetic acid derivative conjugates. J. Med. Chem. 41, 3546-3549.
51. Geoghegan, K. F., Stroh, J. G. (1992) Site-directed conjugation of nonpeptide groups to peptides and proteins via periodate oxidation of a 2-amino alcohol. Application to modofocation at N-terminal serine. Bioconjugate Chem. 3, 138-146.
52. Pearson, D. A., Lister-James, J., McBride, W. J., Wilson, D. M., Martel, L. J., Civitello, E. R., and Dean, R. T. (1996) Thrombus imaging using technetium-99m-labeled high-potency GPIIb/IIIa receptor antagonists. Chemistry and initial biological studies. J. Med. Chem. 39, 1372-1382.
53. Pearson, D. A., Lister-James, J., McBride, W. J., Wilson, D. M., Martel, L. J., Civitello, E. R., Taylor, J. E., Moyer, B. R., and Dean, R. T. (1996) Somatostatin receptor-binding peptides labeled with technetium-99m: chemistry and initial biological studies. J. Med. Chem. 39, 1361-1371.
54. Hnatowich, D. J., Layne, W. W., Childs, R. L., Lanteigne, D., Davis, M. A., Griffin, T. V., and Doherty, P. W. (1983) Radioactive labeling of antibody: A simple and efficient method. Science 220, 613-615.
55. 111In-DTPA-D-Phe]-octreotide, a potential radiopharmaceutical for imaging of somatostatin receptorpositive tumors: synthesis, radiolabeling and in vitro validation. Life Sci. 49, 1583-1591.
56. Krejcarek, G. E., and Tucker, K. L. (1977) Covalent attachment of chelating groups to macromolecules. Biochem. Biophys. Res. Commun. 2, 581-585.
57. 1-octreotide synthesis. Bioconjugate Chem. 8, 442-446.
58. Maecke, H. R., Riesen, A., and Ritter, W. (1989) The molecular structure of Indium-DTPA. J. Nucl. Med. 30, 1235-1239.
59. 111In]DTPA-folate for use as a tumortargeted radiopharmaceutical. Bioconjugate Chem. 8, 673.
60. 0]octreotide. Eur. J. Nucl. Med. 25, 182-186.
61. 111In-DTPA-Octreotide. Pept. Res. 9, 144-150.
62. Brechbiel, M. W., and Gansow, O. A. (1991) Backbone-substituted DTPA ligands for 90Y radioimmunotherapy. Bioconjugate Chem. 2, 187-194.
63. Kobayashi, H., Wu, C., Yoo, T. M., Sun, B. F., Drumm, D., Pastan, I., Paik, C. H., Gansow, C. A., Carrasquilleo, J. A., and Brechbiel, M. N. (1998) Evaluation of the in vivo biodistribution of yttrium-labeled isomers of CHX-DTPA-conjugated monoclonal antibodies. J. Nucl. Med. 39, 829-836.
64. Wu, C., Kobayashi, H., Sun, B., Yoo, T. M., Paik, C. H., Gansow, O. A., Carrasquillo, J. A., Pastan, I., and Brechbiel, M. W. (1997) Stereochemical influence on the stability of radio-metal complexes in vivo. Synthesis and evaluation of the four stereoisomers of 2-(p-nitrobenzyl)-trans-CyDTPA. Bioorg. Med. Chem. 5, 1925-1934.
65. Safavy, A., Smith, D. C., Bazooband, A., and Buchsbaum, D. J. (2002) De novo synthesis of a new diethylenetriaminepentaacetic acid (DTPA) bifunctional chelating agent. Bioconjugate Chem. 13, 317-326.
66. Safavy, A., Smith, D. C., Jr., Bazooband, A., and Buchsbaum, D. J. (2002) Synthesis of the first diethylenetriaminepentahydroxamic acid (DTPH) bifunctional chelating agent. Bioconjugate Chem. 13, 327-332.
67. Blok, D., Feitsma, R. I. J., Vermeij, P., and Pauwels, E. J. K. (1999) Peptide radiopharmaceuticals in nuclear medicine. Eur. J. Nucl. Med. 26, 1511-1519.
68. 3]octreotide, a promising somatostatin analogue for radionuclide therapy. Eur. J. Nucl. Med. 24, 368-371.
69. McMurry, T. J., Brechbiel, M., Kumar, K., and Gansow, O. A. (1992) Convenient synthesis of bifunctional tetraaza macrocycles. Bioconjugate Chem. 3, 108-117.
70. DeNardo, S. J., Kukis, D. L., Miers, L., Winthrop, M. D., Kroger, L. A., Salako, Q., Shen, S., Lamborn, K. R., Gumerlock, P. H., Meares, C. F., and DeNardo, G. L. (1998) Yttrium-90-DOTA-peptide-chimeric L6 radioimmunoconjugate: efficacy and toxicity in mice bearing p53 mutant human breast cancer xenografts. J. Nucl. Med. 39, 842-849.
71. DeNardo, S. J., Zhong, G. R., Salako, Q., Li, M., DeNardom G. L., and Meares, C. F. Pharmacokinetics of chimeric L6 conjugated to indium-111-and yttrium-90-DOTA-peptide in tumor-bearing mice. J. Nucl. Med. 36, 829-836
72. Otte, A., Jermann, E., Behe, M., Goetze, M., Bucher, H. C., Roser, H. W., Heppeler, A., Mueller-Brand, J., and Maecke, H. R. (1997) DOTATOC: a powerful new tool for receptor mediated radionuclide therapy. Eur. J. Nucl. Med. 24, 792-795.
73. Virgolini, I., Szilvasi, I., Kurtaran, A., Angelberger, P., Raderer, M., Havlik, E., Vorbeck, F., Bischof, C., Leimer, M., Dorner, G., Kletter, K., Niederle, B., Scheithauer, W., and Smith-Jones, P. (1998) Indium-111-Dota-lanreotide: biodistribution, safety and radiation absorbed dose in tumour patients. J. Nucl. Med. 39, 1928-1936.
74. Keire, D. A., Jang, Y. H., Li, L., Dasgupta, S., Goddard, W. A., III, and Shively, J. E. (2001) Chelators for radioimmunotherapy: I. NMR and ab initio calculation studies on 1,4,7,10-tetra(carboxyethyl)-1,4,7,10-tetraazacyclododecane (DO4Pr) and 1,4,7-tris(carboxymethyl)-10-(carboxyethyl)-1,4,-10-tetraazacyclododecane (DO3A1Pr). Inorg. Chem. 40, 4310-4318.
75. Otte, A., Mueller-Brand, J., Dellas, S., Nitzsche, E. U., Herrmann, R., and Maecke, H. R. (1998) Yttrium-90-labeled somatostatin-analogue for cancer treatment. Lancet 351, 417-418.
76. Smith-Jones, P., Bischof, C., Leimer, D., Gludovacz, D., Angelberger, P., Pangerl, T., Peck-Radosavljevic, M., Hamilton, G., Kaserer, K., Steiner, G., Schlagbauer-Wadl, H., Maecke, H., and Virgolini, I. (1998) "Mauritius", a novel somatostatin analogue for tumour diagnosis and therapy. J. Nucl. Med. 39 Suppl: 223P.
77. Heppeler, A., Behe, M., Froidevaux, S., Hennig, M., Jermann, E., and Maecke, H. R. (1998) Metal coordination chemical aspects and tumour targeting of a promising somatostatin analogue. J. Nucl. Med. 39 Suppl, 63P.
78. 90Y-SMT 487) eradicates experimental rat pancreatic CA20948 tumours. Eur. J. Nucl. Med. 7, 668-674.
79. Reubi, J. C., Waser, B., Schaer, J. C., Laederach, U., Erion, J., Srinivasan, A., Schmidt, M. A., and Bugaj, J. E. (1998) Unsulfated DTPA- and DOTA-CCK analogues as specific high affinity ligands for CCK-B receptor-expressing human and rat tissues in vitro and in vivo. Eur. J. Nucl. Med. 25, 481-490.
80. Broan, C. J., Cox, J. P. L., Craig, A. S., Kataky, R., Parker, D., Harrison, A., Randall, A. M., and Ferguson, G. (1991) Structure and solution stability of indium and gallium complexes of 1,4,7-triazacyclononanetriacetate and of Ytrium complexes of 1,4,7,10-tetraazacyclododecanetetraacetate and related ligands: Kinetically stable complexes for use in imaging and radioimmunotherapy. X-ray molecular structure of the indium and gallium complexes of 1,4,7-triazacyclononane-1,4,7-triacetic acid. J. Chem. Soc., Perkin Trans. 2, 87-98.
81. Clarke, E. T., and Martell, A. (1991) Stabilities of the Fe-(III), Ga(III) and In(III) chelates of N, N′,N″-triazacyclononanetriacetic acid. Inorg. Chem. Acta 181, 273-280.
82. Eisenwiener, K. P., Prata, M. I., Buschmann, I., Zhang, H. W., Santos, A. C., Wenger, S., Reubi, J. C., and Macke, H. R. (2002) NODAGATOC, a new chelator-coupled somatostatin analogue labeled with [67/68Ga] and [111In] for SPECT, PET and tageted therapeutic applications of somatostatin receptor (hsst2) expressing tumors. Bioconjugate Chem. 13, 530-541.
83. Abrams, M. J., Juweid, M., tenKate, C. I., Schwartz, D. A., Hauser, M. M., Gaul, F. E., Fuccello, A. J., Rubin, R. H., Strauss, H. W., and Fischman, A. J. (1990) Technetium-99m.-human polyclonal IgG radiolabeled via the hydrazino nicotinamide derivative for imaging focal sites of infection in rats. J. Nucl. Med. 31, 2022-2028.
84. Schwartz, D. A., Abrams, M. J., Hauser, M. M., Gaul, F. E., Larsen, S. K., Rauh, D., and Zubieta, J. A. (1991) Preparation of hydrazino-modified proteins and their use for the synthesis of 99mTc-protein conjugates. Bioconjugate Chem. 2, 333-336.
85. Babich, J. W., Solomon, H., Pike, M. C., Kroon, D., Graham, W., Abrams, M. J., Tompkins, R. G., Rubin, R. H., and Fischman, A. J. (1993) Technetium-99m-labeled hydrazino nicotinamide derivatized chemotactic peptide analogues for imaging focal sites of bacterial infection. J. Nucl. Med. 34, 1964-1974.
86. Babich, J. W., and Fischman, A. J. (1995) Effect of "coligand" on the biodistribution of 99mTc-labeled hydrazino nicotinic acid derivatized chemotactic peptides. Nucl. Med. Biol. 22, 25-30.
87. 99m.Tc] complex. Liebigs. Ann. 1463-1469.
88. Bangard, M., Behe, M., Guhlke, S., Otte, R., Bender, H., Maecke, H., and Biersack, H.-J. (1998) Detection of somatostatin receptor-positive tumours using the new 99m-Tc-tricine-HYNIC-d-Phe1-Tyr3-octreotide: first results in patients and comparison with 111In-DTPA-d-Phe1-octreotide. Eur. J. Nucl. Med. 27, 628-637.
89. Decristoforo, C., and Mather, S. J. (1999) Technetium-99m somatostatin analogues: effect of labeling methods and peptide sequence. Eur. J. Nucl. Med. 26, 869-876.
90. Decristoforo, C., Melandez-Alafort, L., Sosabowski, J. K., and Mather, S. J. (2000) 99mTc-HYNIC-[Tyr3]-octreotide for imaging somatostatin-receptor-positive tumors: preclinical evaluation and comparison with 111In-octreotide. J. Nucl. Med. 41, 1114-1119.
91. 99mTc. Bioconjugate Chem. 8, 146-154.
92. 99mTc-labeling of hydrazino nicotinamide-modified biologically active molecules using imine-N-containing heterocycles as coligands. Bioconjugate Chem. 9, 583-595.
93. Barrett, J. A., Crocker, A. C., Damphousse, D. J., Heminway, S. J., Liu, S., Edwards, D. S., Lazewatsky, J. L., Kagan, M., Mazaika, T. J., and Carroll, T. L. (1997) Biological evaluation of thrombus imaging agents utilizing water soluble phosphines and tricine as coligands when used to label a hydrazinonicotinamide-modified cyclic glycoprotein IIb/IIIa receptor antagonist with 99mTc. Bioconjugate Chem. 8, 155-160.
94. 3S triamidethiols as bifunctional chelating agents for labeling small peptides with technetium-99m. In Technetium and Rhenium in Chemistry and Nuclear Medicine 4 (Nicolini M., Banoli G., Mazzi U., Eds.) pp 383-393, SG Editoriali, Padova.
95. Najafi, A., Alauddin, M. M., Siegel, M. E., and Epstein, A. L. (1991) Synthesis and preliminary evaluation of a new chelate N2S4 for use in labeling proteins with metallic radionuclides. Int. J. Rad. Appl. Instrum. B. 18, 179-185.
96. Najafi, A., Alauddin, M. M., Sosa, A., Ma, G. Q., Chen, D. C., Epstein, A. L., and Siegel, M. E. (1992) The evaluation of 186Re-labeled antibodies using N2S4 chelate in vitro and in vivo using tumor-bearing nude mice. Int. J. Rad. Appl. Instrum. B. 19, 205-212.
97. Kasina, S., Rao, T. N., Srinivasan, A., Sanderson, J. A., Fitzner, J. N., Reno, J. M., Beaumier, P. L., and Fritzberg, A. R. (1991) Development and biologic evaluation of a kit for preformed chelate technetium-99m radiolabeling of an antibody Fab fragment using a diamide dimercaptide chelating agent. J. Nucl. Med. 32, 1445-1451.
98. Wong, E., Fauconnier, T., Bennett, S., Valliant, J., Nguyen, T., Lau, F., Lu, L. F. L., Pollak, A., Bell, R. A., and Thornback, J. R. (1997) Rhenium(V) and Technetium(V) Oxo Complexes of an N(2)N′S Peptidic Chelator: Evidence of Interconversion between the Syn and Anti Conformations. Inorg. Chem. 36, 5799-5808.
99. Mathias, C. J., Sun, Y., Welch, M. J., Green, M. A., Thomas, J. A., Wade, K. R., and Martell, A. E. (1988) Targeting radiopharmaceuticals: comparative biodistribution studies of gallium and indium complexes of multidentate ligands. Int. J. Rad. Appl. Instrum. B.15, 69-81.
100. Guhlke, S., Schaffland, A., Zamora, P. O., Sartor, J., Diekmann, D., Bender, H., Knapp, F. F., and Biesack, H. J. (1998) 188Re- and 99mTc-MAG3 as prosthetic groups for labeling amines and peptides: approaches with pre- and postconjugate labeling. Nucl. Med. Biol. 25, 621-631.
101. Gano, L., Patricio, L., Marques, E., Cantino, G., Pena, H., Martins, T., and Hnatowich, D. J. (1998) Human polyclonal immunoglobulin labeled with technetium-99m via NHS-MAG3: a comparison of radiochemical behavior and biological efficacy with other labeling methods. Nucl. Med. Biol. 25, 395-403.
102. Benshafrut, R., Haran, A., Shvarts, D., and Schneider, B. (2002) Synthesis and characterization of a new tetradentate ligand for Cu(II) metal ions. J. Org. Chem. 67, 4040-4044.
103. Firestone, R. B. (1996) Table of isotopes (Shirley, W. S., Ed.), Horizon Pubs & Distributors Inc.,
104. Linder, M. C. (1991) Biochemistry of copper, Plenum Press, New York.
105. Goethals, P., Coene, M., Slegers, G., Agon, P., Deman, J., and Schelstraete, K. (1988) Cyclotron production of carrier-free 66Ga as a positron emitting label of albumin colloids for clinical use. Eur. J. Nucl. Med. 14, 152-154.
106. Loc'h, C., Maziere, B., and Comar, D. (1980) A new generator for ionic gallium-68. J. Nucl. Med. 21, 171-173.
107. Herzog, H., Rosch, F., Stocklin, G., Lueders, C., Quaim, S. M., and Feinendegen, L. E. (1993) Measurement of pharmacokinetics of yttrium-86 radiopharmaceuticals with PET and radiation dose calculation of analogous yttrium-90 radiotherapeutics. J. Nucl. Med. 34, 2222-2226.
108. Wester, H. J., Brockmann, J., Rosch, F., Wutz, W., Herzog, H., Smith Jones, P., Stolz, B., Bruns, C., and Stocklin, G. (1997) PET-pharmacokinetics of 18F-octreotide: a comparison with 67Ga-DFO- and 86Y-DTPA-octreotide. Nucl. Med. Biol. 24, 275-286.
109. Rosch, F., Herzog, H., Stolz, B., Brockmann, J., Kohle, M., Muhlensiepen, H., Marbach, P., and Muller-Gartner, H. W. (1999) Uptake kinetics of the somatostatin receptor ligand [86Y]DOTA-DPhe1-Tyr3-octreotide ([86Y]SMT487) using positron emission tomography in nonhuman primates and calculation of radiation doses of the 90Y-labeled analogue. Eur. J. Nucl. Med. 26, 358-366.
110. Sattelberger, A. P., and Atcher, R. W. (1999) Nuclear medicine finds the right chemistry. Nat. Biotechnol. 17, 849-850.
111. Hu, F., Cutler, C. S., Hoffman, T., Sieckman, G., Volkert, W. A., and Jurisson, S. S. (2002) Pm-149 DOTA bombesin analogues for potential radiotherapy, in vivo comparison with Sm-153 and Lu-177 labeled DO3A-amide-betaAla-BBN(7-14)NH(2). Nucl. Med. Biol. 29, 423-430.
112. Signore, A. (1995) Receptor ligands. Q. J. Nucl. Med. 39, 83-85.
113. Bakker, W. H., Krenning, E. P., and Breeman, W. A. (1990) Receptor scintography with a radiolabeled somatostatin analog: radiolabeling, purification, biological activity and in vivo application in animals. J. Nucl. Med. 31, 1501-1509.
114. Bangard, M., Behe, M., and Bender, H. (1998) Technetium-99m-octreotide for the detection of somatostatin receptor positive (SSTR+) tumors: preliminary results. Eur. J. Nucl. Med. 25, 837.
115. Maecke, H. R., Heppeler, A., and Nock, B. (1999) Somatostatin Analogues Labeled with Different Radionuclides. Technetium, Rhenium and Other Metals in Chemistry and Nuclear Medicine 5 (M. Nicolini, U. Mazzi, Eds.) pp 77-91, SGEditoriali, Padova.
116. Thakur, M. L., Kolan, H. R., and Rifat, S. (1996) Vapreotide labeled with 99m-technetium for imaging tumors: preparation and preliminary evaluation. Int. J. Oncol. 9, 445-451.
117. 99mTc. Technetium, Rhenium and Other Metals in Chemistry and Nuclear Medicine 5 (M. Nicolini, U. Mazzi, Eds.) pp 77-91, SGEditoriali, Padova.
118. Thakur, M. L., Eshbach, J., Wilder, S., John, E., and McDevitt, M. R. (1993) Tc-99m labeled Sandostatin: Preparation and preliminary evaluation. J. Label. Compds. Radiopharm. 32, 365-367.
119. Baidoo, K. E., Lin, K. S., Zhan, Y. G., Finley, P., Scheffel, U., and Wagner, H. N., Jr. (1998) Design, synthesis and initial evaluation of high-affinity technetium bombesin analogues. Bioconjugate Chem. 9, 218-225.
120. Rao, P. S., Thakur, M. L., Pallela, V. R., Patti, R., Reddy, K., Li, H., Sharma, S., Pham, H. L., Diggles, L., Minami, C., and Marcus, C. S. (2001) 99mTc labeled VIP analog: evaluation for imaging colorectal cancer. Nucl. Med. Biol. 28, 445-450.
121. 99mTc-labeled vasoactive intestinal peptidereceptor agonist: functional studies. J. Nucl. Med. 40, 352-360.
122. Virgolini, I., Kurtaran, A., and Raderer, M. (1995) Vasoactive intestinal peptide receptor scintigraphy. J. Nucl. Med. 36, 1732-1739.
123. Sivolapenko, G. B., Skarlos, D., and Pectasides, D. (1998) Imaging of metastatic melanoma utilising a technetium-99m labeled RGD-containing synthetic peptide. Eur. J. Nucl. Med. 25, 1383-1389.
124. Varner, J. A., and Cheresh, D. A. (1996) Integrins and cancer. Curr. Opin. Cell. Biol. 8, 724-730.
125. Chen, J., Cheng, Z., Hoffman, T. J., Jurisson, S. S., and Quinn, T. P. (2000) Melanoma-targeting properties of (99m)-technetium-labeled cyclic alpha-melanocyte-stimulating hormone peptide analogues. Cancer Res. 60, 5649-5658.
126. Chen, J., Giblin, M. F., Wang, N., Jurisson, S. S., and Quinn, T. P. (1999) In vivo evaluation of 99mTc/188Re-labeled linear alpha-melanocyte stimulating hormone analogues for specific melanoma targeting. Nucl. Med. Biol. 26, 687-693.
127. van Hagen, P. M., Breeman, W. A., Reubi, J. C., Postema, P. T., van der Anker-Lugtenburg, P. J., Kwekkeboom, D. J., Laissue, J., Waser, B., Lamberts, S. W., Visser, T. J., and Krenning, E. P. Visualization of the thymus by substance P receptor scintigraphy in man. Eur. J. Nucl. Med. 23, 1508-1513.
128. Breeman, W. A., van Hagen, P. M., Visser-Wisselaar, H. A., van der Pluijm, M. E., Koper, J. W., SetyonoHan, B., Bakker, W. H., Kwekkeboom, D. J., Hazenberg, M. P., Lamberts, S. W., Visser, T. J., and Krenning, E. P. (1996) In vitro and in vivo studies of substance P receptor expression in rats with the new analogue [Indium-111-DTPA-Arg1]-substance P. Eur. J. Nucl. Med. 37, 108-117.
129. Babich, J., Graham, W., Barrow, S. A., Fischman, A. J. (1995) Comparison of the infection imaging properties of a 99mTc labeled chemotactic peptide with 111In IgG. Nucl. Med. Biol. 22, 643-648.
130. Babich, J. W., Graham, W., Barrow, S. A., Dragotakes, S. C., Tompkins, R. G., Rubin, R. H., and Fischman, A. J. (1993) Technetium-99m-labeled chemotactic peptides: comparison with indium-111-labeled white blood cells for localizing acute bacterial infection in the rabbit. J. Nucl. Med. 34, 2176-2181.
131. Moerlein, S. M., Welch, M. J., and Hotchkiss, R. M. (1993) A gallium-68-labeled chemotactic peptide analogue for imaging focal sites of bacterial infection. J. Labeled. Cmpds. Radiopharm. 32, 426-427.
132. Otte, A., Jermann, E., Behe, M., Bucher, H. C., Roser, H. W., Heppeler, A., Mueller-Brand, J., and Maecke, H. R. (1997) DOTATOC: a powerful new tool for receptor-mediated radionuclide therapy. Eur. J. Nucl. Med. 24, 792-795.
133. de Jong, M., Bakker, W. H., Breeman, W. A. P., Hofland, L. J., Visser, T. J., Srinivasan, A., Schmidt, M., Behe, M., Maecke, H., and Krenning, E. P. (1998) Pre-clinical comparison of [DTPA0] octreotide, [DTPA0, Tyr3] octreotide and [DOTA0, Tyr3] octreotide as carriers for somatostatin receptor-targeted scintigraphy and radionuclide therapy. Int. J. Cancer 5, 406-411.
134. Krenning, E. P., Kwekkeboom, D. J., Bakker, W. H., Breeman, W. A., Kooij, P. P., Oei, H. Y., van Hagen, M., Postema, P. T., de Jong, M., and Reubi, J. C. (1993) Somatostatin receptor scintigraphy with [111In-DTPA-D-Phe1]and [123I-Tyr3]-octreotide: the Rotterdam experience with more than 1000 patients. Eur. J. Nucl. Med. 20, 716-731.
135. Heppeler, A., Froidevaux, S., Eberle, A. N., and Maecke, H. R. (2000) Receptor targeting for tumor localisation and therapy with radiopeptides. Curr. Med. Chem. 7, 971-994.
136. de Jong, M., Bernard, B. F., de Bruin, E., van Gameren, A., Bakker, W. H., Visser, T. J., Maecke, H. R., and Krenning, E. P. (1988) Internalization of radiolabeled [DTPA0]octreotide and [DOTA0, Tyr3]octreotide: peptides for somatostatin receptor-targeted scintigraphy and radionuclide therapy. Nucl. Med. Commun. 19, 283-288.
137. Maina, T., Stolz, B., Albert, R., Bruns, C., Koch, P., and Maecke, H. (1994) Synthesis, radiochemistry and biological evaluation of a new somatostatin analogue (SDZ 219-387) labeled with technetium-99m. Eur. J. Nucl. Med. 21, 437-444.
138. Fischman, A. J., Babich, J. W., and Rubin, R. H. (1994) Infection imaging with technetium-99m-labeled chemotactic peptide analogues. Semin. Nucl. Med. 24, 154-168.
139. Bagutti, C., Stolz, B., Albert, R., Bruns, C., Pless, J., and Eberle, A. N. (1993) [111In]DTPA-labeled analogues of alpha-MSH for the detection of MSH receptors in vitro and in vivo. Ann. N.Y. Acad. Sci. 680, 445-447.
140. Bard, D. R. (1995) An improved imaging agent for malignant melanoma, based on [Nle4, D.-Phe7]alpha-melanocyte stimulating hormone. Nucl. Med. Commun. 16, 860-866.
141. Reubi, J. C., Wasser, B., Friess, H., Buchler, M., and Laissue, J. (1998) Neurotensin receptors: a new marker for human ductal pancreatic adenocarcinoma. Gut 42, 546-550.
142. Reubi, J. C., Waser, B., Schaer, J. C., and Laissue, J. (1999) Neurotensin receptors in human neoplasms: high incidence in Ewing's sarcomas. Int. J. Cancer 82, 213-218.
143. Hennig, I. M., Laissue, J. A., Horisberger, U., and Reubi, J. C. (1995) Substance-P receptors in human primary neoplasms: tumoral and vascular localization. Int. J. Cancer 61, 786-792.
144. Fischman, A. J., Pike, M. C., and Kroon, D. (1991) Imaging focal sites of bacterial infection in rats with indium-111-labeled chemotactic peptide analogues. J. Nucl. Med. 32, 483-491.
145. Liu, S., Edwards, D. S., Looby, R. J., Poirier, M. J., Rajopadhye, M., Bourque, J. P., and Carroll, T. R. (1996) Labeling cyclic glycoprotein IIb/IIIa receptor antagonists with 99mTc by the preformed chelate approach: effects of chelators on properties of [99mTc]chelator-peptide conjugates. Bioconjugate Chem. 7, 196-202.
146. Barrett, J. A., Damphousse, D. J., Heminway, S. J., Liu, S., Edwards, D. S., Looby, R. J., and Carroll, T. R. (1996) Biological evaluation of 99mTc-labeled cyclic glycoprotein IIb/IIIa receptor antagonists in the canine arteriovenous shunt and deep vein thrombosis models: effects of chelators on biological properties of [99mTc] chelator-peptide conjugates. Bioconjugate Chem. 7, 203-208.
147. Lamberts, S. W. J. (1988) The role of somatostatin in the regulation of anterior pituitary hormone secretion and the use of its analogues in the treatment of human pituitary tumors. Endocr. Rev. 9, 417-436.
148. Lamberts, S. W. J., Krenning, E. P., and Reubi, J. C. (1991) The role of somatostatin and its analogues in the diagnosis and treatment of tumours. Endocrine Rev. 19, 450-482.
149. Thakur, M. L., Kolan, H., Li, J., Wiaderkiewicz, R., Pallela, V. R., Duggaraju, R., and Schally, A. V. (1997) Radiolabeled somatostatin analogues in prostate cancer. Nucl. Med. Biol. 24, 105-113.
150. de Jong, M., Breeman, W. A. P., and Bernard, H. F. (1999) Therapy of neuroendocrine tumours with radiolabeled somatostatin analogues. Q. J. Nucl. Med. 43, 356-366.
151. 131I-tryosyl somatostatin. Br. J. Radiol. 49, 381-382.
152. Anderson, C. J., Dehdashti, F., Cutler, P. D., Schwarz, S. W., Laforest, R., Bass, L. A., Lewis, J. S., and McCarthy, D. W. (2001) 64Cu-TETA-octreotide as a PET imaging agent for patients with neuroendocrine tumors. J. Nucl. Med. 42, 213-221.
153. Lewis, J. S., Lewis, M. R., Cutler, P. D., Srinivasan, A., Schmidt, M. A., Schwarz, S. W., Morris, M. M., Miller, J. P., and Anderson, C. J. (1999) Radiotherapy and dosimetry of 64Cu-TETA-Tyr3-octreotate in a somatostatin receptor-positive, tumor-bearing rat model. Clin. Cancer Res. 5, 3608-3616.
154. Bauer, W., Briner, U., Doepfner, W., Haller, R., Huguenin, R., Marbach, P., Petcher, T. J., and Pless, J. (1982) SMS 201-995: a very potent and selective octapeptide analogue of somatostatin with prolonged action. Life Sci. 31, 1133-1140.
155. Pless, J., Bauer, W., Briner, U., Doepfner, W., Marbach, P., Maurer, R., Pletcher, T. J., Reubi, J. C., and Vonderscher, J. (1986) Chemistry and pharmacology of SMS 201-995, a long acting octapeptide analogue of somatostatin. Scand. J. Gastroenterol. Suppl. 119, 54-64.
156. Edwards, W. B., Fields, C. G., Anderson, C. J., Pajeau, T. S., Welch, M. J., and Fields, G. B. (1994) Generally applicable, convenient solid-phase synthesis and receptor affinities of octreotide analogues. J. Med. Chem. 37, 3749-3757.
157. McDonald, T. J., Jornvall, J., Nilsson, G., Vagne, M., Ghatei, M., Bloom, S. R., and Mutt, V. (1979) Characterization of a gastrin releasing peptide from porcine nonatral gastric tissue. Biochem. Biophys. Res. Commun. 90, 227-233.
158. Moody, T. W., Carney, D. N., Cuttita, F., Quattrocchi, K., and Minna, J. D. (1985) High affinity receptors for bombesin/GRP-like peptides on human small cell lung cancer. Life Sci. 37, 105-113.
159. Moody, T. W., Mahmoud, S., Staley, J. S., Naldini, L., Cirillo, D., South, V., Felder, S., and Kris, R. (1989) Human glioblastoma cell lines have neuropeptide receptors for bombesin/GRP. J. Mol. Neurosci. 1, 235-242.
160. Yano, T., Pinski, J., Szepeshazi, K., Groot, K., and Schally, A. V. (1992) Stimulation by bombesin/gastrin releasing peptide antagonist RC-3095 of growth of human breast cancer lines. Cancer Res. 52, 4545-4547.
161. Breeman, W. A., Hofland, L. J., de Jong, M., Bernard, B. F., Srinivasan, A., Kwekkeboom, D. J., Visser, T., and Krenning, E. P. (1999) Evaluation of radiolabeled bombesin analogues for receptor-targeted scintigraphy and radiotherapy. Int. J. Cancer 81, 658-665.
162. Breeman, W. A., de Jong, M., Bernard, B. F., Kwekkeboom, D. J., Srinivasan, A., van der Pluijm, M. E., Hofland, L. J., Visser, T. J., and Krenning, E. P. (1999) Pre-clinical evaluation of [(111)In-DTPA-Pro(1), Tyr(4)]bombesin, a new radioligand for bombesin-receptor scintigraphy. Int. J. Cancer 83, 657-663.
163. Moody, T. W., and Perry, D. C. (1989) Peptide Receptors. Receptor Pharmacology and Function (M. Williams, R. A. Glennon, P. B. M. W. M. Timmermans, Eds.) pp 527-570, Dekker, New York.
164. Pallela, V. R., Reddy, M. V. R., Senadhi, V. K., and Thakur, M. L. (1998) Synthesis and evaluation of Tc-99m-labeled VIP analogues as potential tumour imaging agents. J. Nucl. Med.. 39, 226P.
165. Ali, F. E., Bennett, D. B., Calvo, R. R., and Elliott, J. D. (1994) Conformationally constrained peptides and semipeptides derived from RGD as potent inhibitors of the platelet fibrinogen receptor and platelet aggregation. J. Med. Chem. 37, 769-780.
166. 3 antagonists. J. Med. Chem. 37, 1-8.
167. Teng, W., Rose, J. W., Philips, D. R., Nannizzi, L., Arsen, A., Campbell, A. M., and Charo, I. F. (1993) Design of potent and specific integrin anatagonists. J. Biol. Chem. 268, 1066-1073.
168. Zablocki, J. A., Miyano, M., and Garland, R. B. (1993) Potent in vitro and in vivo inhibitors of platelet aggregation based upon the Arg-Gly-Asp-Phe sequence of fibrinogen. A proposal on the nature of the binding interaction between the Arg-guanidine of RGDX mimetics and the platelet GP IIb/IIIa receptor. J. Med. Chem. 36, 1811-1919.
169. Bach, A. C., Eyermann, C. J., and Gross, J. D. (1994) Structural studies of a family of a high affinity ligands for GPIIb/IIIa. J. Am. Chem. Soc. 116, 3207-3219.
170. Jackson, S., DeGrado, W. F., and Dwivedi, A. (1994) Template-constrained cyclic peptides: design of high affinity ligands for GPIIb/IIIa. J. Am. Chem. Soc. 116, 3220-3230.
171. α-methylarginine-containing peptide. J. Org. Chem. 60, 946-952.
172. Muto, P., Lastoria, S., and Varrella, P. (1995) Detecting deep venous thrombosis with technetium-99m-labeled synthetic peptide P280. J. Nucl. Med. 36, 1384-1391.
173. Lister-James, J., Knight, L. C., Mauer, A. H., Bush, L. R., Moyer, B. R., and Dean, R. T. (1996) Thrombus imaging with technetium-99m-labeled, activated platelet receptor binding peptide. J. Nucl. Med. 37, 775-781.
174. Siegrist, W., Oestreicher, M., Stutz, S., Girard, J., and Eberle, A. N. (1988) Radioreceptor assay for alpha-MSH using mouse B16 melanoma cells+. J Recept. Res. 8, 323-343.
175. Siegrist, W., Solca, F., Stutz, S., Giuffre, L., Carrel, S., Girard, J., and Eberle, A. N. (1989) Characterization of receptors for alpha-melanocyte-stimulating hormone on human melanoma cells. Cancer Res. 49, 6352-6358.
176. Tatro, J. B., Atkins, M., Mier, J. W., Hardarson, S., Wolfe, H., Smith, T., Entwistle, M. L., and Reichlin, S. (1990) Melanotropin receptors demonstrated in situ in human melanoma. J. Clin. Invest. 85, 1825-1832.
177. Chen, J., Giblin, M. F., Wang, N., Jurisson, S. S., and Qiunn, T. P. (1999) In vivo evaluation of 99mTc/188Re-labeled linear alpha-melanocyte stimulating hormone analogues for specific melanoma targeting. Nucl. Med. Biol. 26, 687-693.